GLUTATHIONE ADDUCTS OF N-METHYL-4-AMINOAZOBENZENE FORMED INVIVO AND BY REACTION OF N-BENZOYLOXY-N-METHYL-4-AMINOAZOBENZENE WITH GLUTATHIONE

被引:34
作者
KETTERER, B [1 ]
KADLUBAR, F [1 ]
FLAMMANG, T [1 ]
CARNE, T [1 ]
ENDERBY, G [1 ]
机构
[1] NATL CTR TOXICOL RES,JEFFERSON,AR 72079
基金
英国医学研究理事会;
关键词
D O I
10.1016/0009-2797(79)90065-6
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
N-Benzoyloxy-N-methyl-4-aminoazobenzene (N-BzO-MAB) is believed to be an analogue of the ultimate carcinogenic form of N,N-dimethyl-4-amino-azobenzene (DAB). The reaction of N-BzO-MAB with glutathione in vitro yielded one major and two minor aminoazo dye-glutathione adducts. After purification by ion exchange chromatography and high pressure liquid chromatography, analysis of chemical properties, and the measurement of ultraviolet, visible, proton magnetic resonance, and mass spectra, the major and one minor adduct were identified as 3-(glutathion-S-yl)-N-methyl-4-aminoazobenzene (3-GS-MAB) and 2'-(glutathi on-S-yl)-N-methyl-4-aminoazo-benzene (2'-GS-MAB) respectively. The other minor adduct was tentatively identified as 4'-(glutathion-S-yl)-N-methyl-4-aminoazobenzene (4'-GS-MAB). Fractionation and analyses of biliary metabolites from rats given DAB revealed the presence of two aminoazo dye-glutathione adducts. One of these was identical to 3-GS-MAB in its Chromatographic and chemical properties and its visible and ultraviolet spectra. The other adduct was partially characterized and judged to be a 4-aminoazobenzene-glutathione adduct. The role of glutathione in the detoxification of carcinogenic aminoazo dyes is discussed. © 1979.
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页码:7 / 21
页数:15
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